Water → HCID 19987311, compound

HRID 973964Notes

Reaction equation

HRID 973964 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](/[CH:17]=[CH:18]/[C:19]([NH2:21])=[O:20])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.O>Cl.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH2:18][C:19]([NH2:21])=[O:20])[CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 962WaterHCID 67923539HCID 67923539, compound

Product 1

HCID 19987311HCID 19987311, compoundYield 28.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolvent

Procedure

A solution of the product of stage (ii) (650 mg) in ethanolic hydrogen chloride was hydrogenated over pre-reduced 10% palladium on carbon (0.20 g of a 50% w/w paste with water) at 25° and atmospheric pressure for 24 h. The catalyst was removed by filtration and the solvent evaporated in vacuo to give a foam. The residue was purified by flash column chromatography eluting with dichloromethane:ethanol:0.88 ammonia (50:8:1). Evaporation of the solvent in vacuo from the appropriate fractions gave the title compound as a foam (188 mg).

Workup

  1. customat 25°
  2. customThe catalyst was removed by filtration
  3. customthe solvent evaporated in vacuo
  4. customto give a foam
  5. customThe residue was purified by flash column chromatography
  6. washeluting with dichloromethane
  7. customEvaporation of the solvent in vacuo from the appropriate fractions

Sources & evidence

ORD record
ord-9543c20dbdd94044932c57f0534af32a
Source dataset
uspto-grants-1991_11
Patent number
US05066660

Reaction notes

Loading…